3789-75-1

Basic information

• Product Name: 3-HYDROXY-4-PHENYLAZO-NAPHTHALENE-2-CARBOXYLIC ACID PHENYLAMIDE
• Synonyms: 3-hydroxy-N-phenyl-4-(phenylazo)-2-Naphthalenecarboxaminde;Scarlet 808;Shanghai Bronze Red;3-Hydroxy-N-phenyl-4-(2-phenyldiazenyl)-2-naphthalenecarboxamide
• CAS NO: 3789-75-1
• Molecular Formula: C₂₃H₁₇N₃O₂
• Molecular Weight: 367.4
• Mol File: 3789-75-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 204-205 °C
• Boiling Point: 535.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.23±0.1 g/cm3(Predicted)
• PKA: 10.63±0.50(Predicted)
• CAS DataBase Reference: 3-HYDROXY-4-PHENYLAZO-NAPHTHALENE-2-CARBOXYLIC ACID PHENYLAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-4-PHENYLAZO-NAPHTHALENE-2-CARBOXYLIC ACID PHENYLAMIDE(3789-75-1)
• EPA Substance Registry System: 3-HYDROXY-4-PHENYLAZO-NAPHTHALENE-2-CARBOXYLIC ACID PHENYLAMIDE(3789-75-1)

Safety Data

• Hazardous Substances Data: 3789-75-1(Hazardous Substances Data)

Usage

General Description

3-Hydroxy-4-phenylazo-naphthalene-2-carboxylic acid phenylamide is a chemical compound that is derived from naphthalene. It is a phenylamide derivative of a naphthalene carboxylic acid, and it contains a phenylazo group. 3-HYDROXY-4-PHENYLAZO-NAPHTHALENE-2-CARBOXYLIC ACID PHENYLAMIDE has potential applications in the field of organic synthesis and chemical research. It may also have properties that make it useful in pharmaceutical research, particularly in the development of new drugs. However,

Synthetic route

2,3-oxynaphthoic acid phenylamide (92-77-3) + benzene diazonium chloride (100-34-5) → 1-phenylazo-2-hydroxy-3-phenylcarbamoylnaphthalene (3789-75-1)

Conditions	Yield
With sodium hydroxide at 10℃; for 30h;	94.9%

benzenediazonium (2684-02-8) + 2,3-oxynaphthoic acid phenylamide (92-77-3) → 1-phenylazo-2-hydroxy-3-phenylcarbamoylnaphthalene (3789-75-1)

benzenediazonium (2684-02-8) + 2-hydroxy-3-phenylcarbamoyl-naphthalene-1-sulfonic acid (871874-72-5) → 1-phenylazo-2-hydroxy-3-phenylcarbamoylnaphthalene (3789-75-1)

Conditions	Yield
in alkal. Loesung;

2,3-oxynaphthoic acid phenylamide (92-77-3) → 1-phenylazo-2-hydroxy-3-phenylcarbamoylnaphthalene (3789-75-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitrobenzene; chlorosulfonic acid / 50 - 60 °C 2: in alkal. Loesung View Scheme

1-phenylazo-2-hydroxy-3-phenylcarbamoylnaphthalene (3789-75-1) + methyl iodide (74-88-4) → N-methyl-1-phenylazo-2-methoxy-3-naphthanilide (87407-75-8)

Conditions	Yield
With sodium hydride In dimethyl sulfoxide at 40℃; for 38h;	28.8%

1-phenylazo-2-hydroxy-3-phenylcarbamoylnaphthalene (3789-75-1) + methyl iodide (74-88-4) → 1-phenylazo-2-hydroxy-3-naphtho-N-methylanilide (83038-40-8)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 40 - 42℃;

Upstream product

• 2684-02-8 benzenediazonium 
• 92-77-3 2,3-oxynaphthoic acid phenylamide 
• 871874-72-5 2-hydroxy-3-phenylcarbamoyl-naphthalene-1-sulfonic acid 
• 100-34-5 benzene diazonium chloride 

Downstream Products

• 83038-40-8 1-phenylazo-2-hydroxy-3-naphtho-N-methylanilide 
• 87407-75-8 N-methyl-1-phenylazo-2-methoxy-3-naphthanilide 

Relevant articles and documents

TAUTOMERISM IN THE DERIVATIVES OF 1-PHENYLAZO-2-HYDROXY-3-NAPHTHANILIDE

The spectroscopic criteria for the presence of the azo and quinone hydrazone tautomers were obtained by analysis of the data from electronic spectroscopy and quantum-chemical calculation of the derivatives of 1-phenylazo-2-hydroxy-3-naphthanilide and the fixed forms of the tautomers; the ratio of the azo and quinone hydrazone tautomers depends on the polarity of the solvent; in the transition from chloroform to dimethylformamide the content of the azo form changes from 14.6 to 30.1 percent. "Anomalous" changes in the spectra of 1-arylazo-2-hydroxy-3-naphthanilides compared with the spectra of 1-phenylazo-2-naphthol are brought about by the overlap of the long-wave bands of the azo and quinone hydrazone tautomers with the band for charge transfer from the anilide group to the azo or quinone hydrazone system.